Fumaric Acid → 5-Chloro-thiophene-2-carboxylic acid [2-(1-isopropyl-piperidin-4-ylsulfamoyl)-ethyl]-amide fumarate

HRID 416491Notes

Reaction equation

HRID 416491 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][S:11]([CH2:14][CH2:15][NH:16][C:17]([C:19]2[S:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[O:18])(=[O:13])=[O:12])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29]>CC(C)=O.O>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29].[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][S:11]([CH2:14][CH2:15][NH:16][C:17]([C:19]2[S:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[O:18])(=[O:12])=[O:13])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 119904785-Chloro-Thiophene-2-Carboxylic Acid [2-(1--Isopropyl-Piperidin-4-Ylsulfamoyl)-Ethyl]-Amide

Product 1

HCID 666249505-Chloro-thiophene-2-carboxylic acid [2-(1-isopropyl-piperidin-4-ylsulfamoyl)-ethyl]-amide fumarate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

300 mg (0.76 mmol) of pure 5-chloro-thiophene-2-carboxylic acid [2-(1-isopropyl-piperidin-4-ylsulfamoyl)-ethyl]-amide were dissolved in 1.5 ml acetone. 88.4 mg (1 equiv.) fumaric acid, dissolved in a mixture of 3 ml acetone and 0.1 ml water, were added dropwise. After 48 h the formed precipitate was filtered off and washed with 3 ml cold acetone. The filter residue was dried at 35° C. under vacuo to give crystalline 5-chloro-thiophene-2-carboxylic acid [2-(1-isopropyl-piperidin-4-ylsulfamoyl)-ethyl]-amide fumarate.

Workup

  1. additionwere added dropwise
  2. filtrationAfter 48 h the formed precipitate was filtered off
  3. washwashed with 3 ml cold acetone
  4. customThe filter residue was dried at 35° C. under vacuo

Sources & evidence

ORD record
ord-72c809dd1a0648cd9369d9918d6b7242
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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